The Inside Story On Why Kevin Rose Never Had A Big Hit

Last week, Betaworks, a small, privately held company in New York bought a website called Digg for $500,000.

This was shocking news to the Internet industry.

Just six years ago, Digg was a hot startup fielding big buyout offers. News Corp. wanted to buy it for $60 million. Al Gore took a look at snapping it up for his Current TV channel. A Google deal for around $200 million came agonizingly close to fruition.

But perhaps we shouldn't be surprised at Digg's fate, because its creator—a tech whiz and creative product inventor named Kevin Rose—has a way of creating amazing products and then neglecting them.

You could say his own career is the ultimate example of this cycle of unfulfilled promise.

Colleagues paint a picture of Rose as a brilliant product designer with an uncanny sense for the perfect user experience who was plagued with an utter disinterest in day-to-day activities.

The twilight days of his two biggest projects—an experimental app laboratory called Milk and the news aggregator Digg—are eerily similar, and speak to his core nature.

Below is a chronicling of his days at Digg, Milk, and the times in between, pieced together with interviews with several individuals that have worked with him or know people that have worked with him. Unless specifically named, our sources have asked to remain anonymous. Rose did not respond to a request for comment on this story.

Leaping from backstage to the hot seat at TechTV

Kevin Rose's first gig was actually running cables for TechTV as an IT guy. By chance, he had stumbled onto a golden nugget of information related to Windows security, and was put on camera by TechTV's Leo LaPorte.

Rose was a natural on screen.

As a result, Rose—just a tech junkie with a little bit of drive—was hired as a production assistant for one of the most influential shows in technology at the time in 1998.

Leo LaPorte first discovered Kevin Rose, putting him on TV.

Shortly after that he met Jay Adelson—whom he brought on to TV for a segment on one of Adelson's companies.

Rose always wanted to be an entrepreneur. Adelson, a tech-company founder with a background in film and broadcasting, always wanted to produce segments.

It was a perfect match. Adelson became a mentor to Rose, and Rose would often stay with Adelson and his family in New York.

Adelson spent some time consulting and mentoring Rose, encouraging him to build a prototype of the site.

The drive and passion of Rose was hard to resist and eventually, Adelson caved, and joined Rose full-time on Digg.

BusinessweekPreserved in infamy: the profile that catapulted Kevin Rose to media superstardom.

Becoming King of the Internet

Rose became a media darling thanks to the swift success of Digg, which captured the minds of a young segment of tech-savvy teens and twentysomethings who spent hours voting headlines up and down.

TechTV went off the air after Comcast acquired it and folded it into another cable channel, but Rose found another outlet: Revision3, another startup he and Adelson cofounded. Its lead broadcast: Diggnation, Rose's take on the top headlines on Digg. He and cohost Alex Albrecht frequently drank beer during episodes—a mild style of bad-boy behavior that endeared him to millions of online fans.

As a result of Digg and Diggnation, his intertwined enterprises, Rose was a magnet for fresh, young Web talent that looked up to him and dreamed of making millions by turning Rose's brilliant ideas into reality.

Rose wasn't even 30 years old. He already had two of the hottest properties on the Web. Rosemania hit critical mass after BusinessWeek put him on the cover.

All along, Rose maintained that he wasn't in it for the fame—that he just wanted to design products. But hiring a bunch of true-believer fans inevitably had an effect.

Jay Adelson was an early mentor of Rose, and became CEO of Digg.

"He didn't surround himself with older, wiser people," a colleague said. "He wanted to surround himself with people who adored him, and I think that was probably a weakness, not finding someone who could say no."

Rose had Adelson, it's true, and advisors like experienced tech exec Brett Bullington and David Sze of Greylock Partners. But he never took enough advantage of their advice.

For a while, though, the Digg crew was unstoppable. With Rose fully engaged, the site rocketed to tens of millions of users.